search location
Travel Dates:
Reset Dates
769 Rentals In Bennington Area
United States
Vermont
Bennington Area
Filters
Sub Areas
Green Mountain National Forest
(40)
Green Mountain National Forest
(40)
Emerald Lake
(1)
Dorset
(1)
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Christmas - New Years! Founders Lodge mountain view condo. Short walk to lifts.
4
3.0
13
Stratton Vermont Condo
Click For Pricing
Stunning VT Farmhouse minutes to Stratton\/Bromley
4
2.0
12
Londonderry Vermont Private vacation home
From $500 per night
(USD)
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
1
1.0
8
Shaftsbury Vermont Private vacation home
From $207 per night
(USD)
Stratton Mountain Townhouse - Great Location For Ski Families!
3
3.0
8
Stratton Vermont Condo
From $1000 per night
(USD)
Mountain views. Ski Bromely, Stratton. Minutes to restaurants, Equinox, Ekwanok.
3
3.0
6
Manchester Vermont Private vacation home
From $412 per night
(USD)
Stratton Trailside Condo
3
3.0
8
Winhall Vermont Condo
From $825 per night
(USD)
AFFORDABLE, CHARMING, DORSET GETAWAY. PET FRIENDLY. CLOSE TO THE HORSE SHOW.
2
1.0
4
Dorset Vermont Private vacation home
From $185 per night
(USD)
Seven Springs House Nestled in the Heart of Dorset
5
6.0
12
Dorset Vermont Private vacation home
Click For Pricing
A luxury cottage in the heart of Manchester Center
1
1.0
2
Manchester Center Vermont Cottage
From $389 per night
(USD)
NO LONG TERM RENTALS - Located across the street from the Lower Wanderer Trail
5
4.0
14
Stratton Vermont Chalet
From $1800 per night
(USD)
Special lovely home for wedding, shopping, hiking, golfing, skiing and reunions
5
5.0
10
Manchester Vermont Private vacation home
From $292 per night
(USD)
Long Trail, Walk to Lifts
1
1.0
4
Stratton Mountain Vermont Condo
From $700 per night
(USD)
Cozy Vermont ski house conveniently located between Stratton and Bromley Mtn.
5
2.0
11
Winhall Vermont Private vacation home
From $500 per night
(USD)
7 Bedroom, 6 Bathroom Manchester Ctr, Mountain View, Hot Tub, and Private Pool
7
6.0
16
Manchester Center Vermont Private vacation home
From $1271 per night
(USD)
StylesBrook Townhouse - Great Location for Ski Families!
4
4.0
8
Stratton Mountain Vermont Private vacation home
From $964 per night
(USD)
Ski In\/ Ski Out. Steps To The Lifts
2
2.0
6
Stratton Vermont Condo
From $133 per night
(USD)
A Beautiful Historic Home in the heart of Manchester Center
5
3.0
12
Manchester Center Vermont Private vacation home
From $871 per night
(USD)
400 FT TO THE LIFT! IN STRATTON VILLAGE @ LANDMARK! COMES W\/ 25% OFF LIFT TIX!
3
2.0
10
Stratton Mountain Vermont Condo
From $293 per night
(USD)
Great House Great Location. Perfect for Families. Stratton,Bromley, Manchester
5
4.0
12
Bondville Vermont Private vacation home
From $338 per night
(USD)
Adjacent to Village\/Walking Distance To Ski Lifts
1
1.0
5
Stratton Vermont Condo
From $680 per night
(USD)
Getaway to the green mountain
3
3.0
10
Manchester Vermont Private vacation home
From $354 per night
(USD)
3 Mountain View home minutes to Stratton\/Bromley
6
5.0
18
winhall Vermont Private vacation home
From $540 per night
(USD)
Great Village location to enjoy all the summer events in the Mancheste area.
3
3.0
6
Arlington Vermont Private vacation home
From $167 per night
(USD)
Manchester Center Home w\/ Green Mtn Views!
2
2.0
4
Manchester Center Vermont Private vacation home
From $218 per night
(USD)
Guest House with stunning views from wrap-around deck
2
2.0
4
Dorset Vermont Guest house
From $225 per night
(USD)
6 bed 7 Bath VT retreat - rent a former B&B Greybourne House, Manchester VT
6
7.0
14
Manchester Center Vermont Private vacation home
From $929 per night
(USD)
Best Location on Stratton Mountain!!
1
1.0
6
Stratton Vermont Condo
From $900 per night
(USD)
*Shred Shack* Hot Tub w\/ Majestic Valley Views
4
3.0
12
Winhall Vermont Private vacation home
From $405 per night
(USD)
Private and Artistic cabin, Pet friendly, no cleaning fee
2
4.0
7
West Pawlet Vermont Cabin
From $200 per night
(USD)
Owners Own Unit on Bromley Mountain - gorgeous views yet close to Manchester
3
3.0
6
Peru Vermont Condo
Click For Pricing
True Vermont Experience! Spectacular home great for ski loving families!
4
3.0
10
Jamaica Vermont Private vacation home
Click For Pricing
Beautiful Vermont Vacation Home- Mount Snow!
4
2.0
10
Wilmington Vermont Private vacation home
From $350 per night
(USD)
4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!
4
2.0
8
Wilmington Vermont Private vacation home
From $170 per night
(USD)
5 Star Rated. Small dogs allowed
1
1.0
4
Stratton Vermont Apartment
From $383 per night
(USD)
Located At Bromley Mountain
3
3.0
8
Peru Vermont Condo
From $331 per night
(USD)
Stratton Mountain, Nearly Ski In\/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath
2
1.0
4
Stratton Vermont Condo
From $300 per night
(USD)
Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
4
3.0
10
Rupert Vermont Private vacation home
From $450 per night
(USD)
Modern 5BR VT home minutes to Stratton w\/ Sauna
5
3.0
12
Jamaica Vermont Private vacation home
From $657 per night
(USD)
Stratton home with spectacular mountain view and hot tub!
5
3.0
12
Winhall Vermont Private vacation home
From $560 per night
(USD)
Newly Designed Chalet w\/Views, Minutes to Stratton
3
2.0
8
Jamaica Vermont Chalet
From $465 per night
(USD)
Bennington Cabin w\/ Deck & Views of 3 States!
2
2.0
6
Bennington Vermont Cabin
From $366 per night
(USD)
Cheerful 4-bedroom chalet close to Ski slopes
4
2.0
8
Peru Vermont Chalet
From $287 per night
(USD)
Stratton South Long Trail Studio Adjacent to the Village and Lifts
1.0
4
Stratton Vermont Apartment
From $160 per night
(USD)
Cozy & Convenient Ski In\/Out Bromley Condo. Steps to Trail!
3
2.0
9
Peru Vermont Condo
From $300 per night
(USD)
STRATTON MOUNTAIN SKI IN\/OUT Tamarack lift
2
2.0
6
Stratton Vermont Condo
From $300 per night
(USD)
Private Centrally Located 3 BR 2 1\/2 Bath 1950Sq' Open Main Floor Space!!!!
3
3.0
8
Winhall Vermont Private vacation home
From $350 per night
(USD)
Cozy ski home with amazing views of Stratton & Bromley Mountains.
4
2.0
11
Winhall Vermont Private vacation home
From $600 per night
(USD)
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
1
2.0
4
Manchester Vermont Cottage
From $229 per night
(USD)
Luxurious Rustic Contemporary in Solitude
5
4.0
14
Peru Vermont Private vacation home
From $431 per night
(USD)
Luxury Custom Built Post and Beam
5
6.0
16
Peru Vermont Private vacation home
From $1491 per night
(USD)
Ski House at Stratton Mountain
5
3.0
12
Winhall Vermont Private vacation home
Click For Pricing
Bennington Guest Farm
5
2.0
9
Bennington Vermont Private vacation home
From $225 per night
(USD)
1920's Bennington Vermont Guest Barn
3
1.0
7
Bennington Vermont Private vacation home
From $150 per night
(USD)
Stratton Mountain Chalet Style Loft
4
2.0
8
Winhall Vermont Chalet
From $229 per night
(USD)
Luxury home in the heart of Manchester. Walk to shops; minutes to mountains.
4
5.0
9
Manchester Vermont Private vacation home
From $917 per night
(USD)
2B\/2b Family friendly condo in Stratton Landmark
2
2.0
10
Stratton Vermont Condo
From $350 per night
(USD)
Hike In\/Hike Out VTFun
3
2.0
6
Peru Vermont Condo
From $248 per night
(USD)
Relax in Vermont: gorgeous views, a pond, gazebo, and sheep! A beautiful spot!
4
3.0
5
West Pawlet Vermont Private vacation home
From $325 per night
(USD)
Vermont Summer Festival Property, 5 Stalls and riding trails
2
2.0
8
Pawlet Vermont Private vacation home
From $600 per night
(USD)
Slope side Stratton Condo - fully equipped and perfect for families
4
4.0
10
Stratton Vermont Private vacation home
From $1629 per night
(USD)
Downtown Victorian House
1
1.0
4
Bennington Vermont Apartment
From $199 per night
(USD)
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
2
2.0
5
Dorset Vermont Cottage
From $349 per night
(USD)
Two-story, spacious, dog-friendly house w\/mountain views & large front porch
5
4.0
13
Londonderry Vermont Private vacation home
From $280 per night
(USD)
Mountain chalet close to Manchester Center
3
2.0
6
Winhall Vermont Chalet
Click For Pricing
Luxury Oasis w\/Serene Views! Close to Ski Slopes w\/Shuttle. Gameroom. Golf. WiFi
6
4.0
16
Winhall Vermont Private vacation home
From $400 per night
(USD)
The Nest at Birch Quarry
4
2.0
8
Dorset Vermont Private vacation home
From $395 per night
(USD)
Lake life at Woodford Cottage
2
1.0
7
Bennington Vermont Cottage
From $186 per night
(USD)
New Custom Log Home 3BR, Loft, 2.5 Bath, Sleeps 8
3
3.0
8
Searsburg Vermont Chalet
From $625 per night
(USD)
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
3
2.0
8
Winhall Vermont Private vacation home
From $240 per night
(USD)
The Franklin luxury Chalet with two fireplaces & guest house. Walk to Equinox.
6
4.0
11
Manchester Vermont Private vacation home
From $809 per night
(USD)
Luxury Living High Above the Center of Town.
2
2.0
6
Bennington Vermont Apartment
From $187 per night
(USD)
The Bear Ski House - 5 mins from Stratton Mountain
6
3.0
16
Winhall Vermont Private vacation home
From $760 per night
(USD)
Modern Ski Chalet 10 mins from Stratton & Bromley
4
2.0
8
Winhall Vermont Private vacation home
From $373 per night
(USD)
School Street House in heart of Manchester Center
5
4.0
12
Manchester Vermont Private vacation home
From $636 per night
(USD)
Perfect House for Leaf Peeping.
3
2.0
8
Winhall Vermont Chalet
From $338 per night
(USD)
**Stratton's Best Kept Secret** Ski On\/Off ** Unit E
2
1.0
4
Stratton Vermont Condo
From $479 per night
(USD)
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
4
3.0
12
Wilmington Vermont Private vacation home
From $361 per night
(USD)
Stratton Mtn. Ski In\/Ski Out OberTal 'F' Bldg 2 Bedrm, 1 Bth.
2
1.0
4
Stratton Mountain Vermont Condo
From $232 per night
(USD)
Secluded Estate with Private Lake, Swimming Pool and Hot Tub
9
6.0
24
Peru Vermont Private vacation home
From $1568 per night
(USD)
Cool Barn reno with views. 5 mins to hike, restaurants, fishing...
1
1.0
2
Manchester Vermont Private vacation home
From $191 per night
(USD)
Luxury Stratton-Area Mountain House minutes from the lodge
4
3.0
11
Winhall Vermont Private vacation home
From $1256 per night
(USD)
Breaktime - Quiet and Private on dead end street
4
2.0
10
Manchester Vermont Private vacation home
From $383 per night
(USD)
Centrally located condo…minutes from major ski resorts.
3
3.0
8
Manchester center Vermont Condo
From $209 per night
(USD)
Hillside Haven- Weekly + Monthly Discounts Available!
3
2.0
10
Wilmington Vermont Private vacation home
From $219 per night
(USD)
Peaceful Summer Getaway Cozy Mountain Condo
1
2.0
4
Peru Vermont Condo
From $236 per night
(USD)
Spectacular Green Mountain views, walk to pool and charming Manchester village
3
3.0
6
Manchester Depot Vermont Private vacation home
From $227 per night
(USD)
Three Maple Drive Contemporary with Beautiful Views
4
3.0
8
Manchester Vermont Private vacation home
From $643 per night
(USD)
Stratton Mountain Condo Close to Main Base & Village - Perfect Family Vacation!
2
2.0
6
Stratton Vermont Condo
Click For Pricing
Feel Right At Home... While Being A Spectator Of Nature.
4
3.0
8
Manchester Center Vermont Private vacation home
From $400 per night
(USD)
Brian Piece of Heaven for fall Foliage. Beautiful colors
1
1.0
4
arlington vt Chalet
From $125 per night
(USD)
Dog-Friendly Two-Story House w\/Free WiFi, Wood Fireplace, Gas Grill, Jetted Tub
4
3.0
9
Stratton Vermont Private vacation home
From $346 per night
(USD)
Beat the Heat, Head to the Mountains!
4
3.0
8
Manchester Vermont Condo
From $183 per night
(USD)
MLK WEEKEND DISCOUNT! Fireside Fun. Ski vacations & Family Reunion dream house: Huge covered deck, double height ceilings, great hang out space. Dogs welcome.
6
3.0
12
Manchester Vermont Private vacation home
From $806 per night
(USD)
Beautiful home near Manchester and the Mountains -
3
2.0
8
Sunderland Vermont Private vacation home
From $300 per night
(USD)
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
6
4.0
18
Winhall Vermont Chalet
From $340 per night
(USD)
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
1
1.0
6
Pownal Vermont Apartment
From $167 per night
(USD)
Adventure Home: Trails, Pool, Gym & Tennis Access
3
2.0
8
Peru Vermont Condo
From $433 per night
(USD)
Bromley Village Condo With Shuttle Service
3
3.0
8
Peru Vermont Condo
Click For Pricing
Green Mountain Retreat. Explore. Discover. Connect.
3
2.0
5
East Dorset Vermont Cabin
From $450 per night
(USD)
Enchanted Mountain House
4
2.0
8
East Dorset Vermont Private vacation home
Click For Pricing
Load More Results
